The Unattainable Valentine
by ggfan19
Summary: Set as if the five year flash forward didn't happen. Chuck and Blair exchanged vows but the marriage didn't survived. Fifteen years following their divorce they meet again. Told from Chuck's point of view.
1. Chapter 1

The Unattainable Valentine

I myself am not an old man. My joints don't hurt when it's cold, my hands don't cramp up from typing, I am familiar with the latest technology infrastructure and my hair isn't completely gray. I am not however, a young man either. I have lived long enough to recognize the many mistakes I have made, the decisions that resulted in consequences; good and bad, and most importantly I recognize that I had and have also lost the unattainable dream. It's a dream that I think of often, constantly replaying the reel in my mind.

Through age comes experience. During my youth I never believed in romantic clichés and common theories. "Things happen for a reason" and "its better to have lost then never loved" are cruel, hurtful phrases written by those who have never experience true loss, and have only seen it in printed work and in the cinema. However, the saying "Things happen when you least expect them" is unfortunately entirely accurate.

I had spent the afternoon picking out cards for the upcoming holiday and therefore reminiscing as I often do, never expecting that my next errand would have me standing right in front of my first and only valentine.

I hadn't seen her in fifteen years. I knew when we said goodbye that it would be a long time before I ever saw her again, but I never thought it would be fifteen years. In many ways she looked exactly the same as I remembered her. As a teenager she never dressed in the typical uniform of girls her own age, she'd opt for classic pieces and cuts like shift dresses, button down blouses, ballet flats, and pencil skirts instead of the typical ripped jeans with holes, ugg boots and baby tees. And in many respects nothing had changed. She still was a petite woman with pale complexion, dressed in head to toe black that mirrored the style of a young Audrey Hepburn in a simple black dress, trench coat and heels. She still carried her life with her in a trendy over-sized handbag, and a small headband rested on top of her head. I'd recognize her anywhere, for her influence during my youth was the reason I became the man I am today.

However, upon further glance there were many subtle differences in her appearance. Her brown hair, no longer light, long and curly, was now dark and rested at her shoulders. Instead of big designer necklaces wrapped around her neck, glasses were tucked into her blouse, real eye glasses. Her eyes had subtle bags under them, most likely a symptom of exhaustion and there were slight creases in the corners of her mouth from laughing over forty years. Her left hand no longer displayed her custom Harry Winston engagement ring with matching wedding and eternity bands to compliment the piece. Instead, her right hand displayed another ring I recognized from two decades prior. A giant smoky topaz ring, that once sat on the hand of her mother, who passed almost ten years ago.

Most importantly she had a frown on her face, something I saw when we were married, only when I disappointed her, which I tried to do sparingly but unfortunately did a lot of during our final year together.

The man with her, was nothing like the man I thought she'd end up with. For starters, it wasn't my former best friend, that faithfully swooped in to collect the pieces of her broken heart after I had mucked up our relationship and left her to deal with the social consequences of my actions. They had, had an on and off relationship for six years, never fully committing to each other, but neither committing to anyone else either. I would have bet everything I owned, including the shirt on my back that she would have ended up with him. But my former friend mucked everything up too. I was told in passing by my step-mother that they had tried to make it work, but his eyes were always lingering on her best friend, and she didn't really care, her heart was never fully committed. The final straw was when he failed to show up when her mother passed away. As a result she closed her heart to him, never forgiving him for letting her down in her darkest hour. Through it all I still keep in touch with him. He's divorced, living here in New York, managing to keep afloat his publishing firm. He even apologized for his pursuit of her.

I was told by my step-sister that her current beau had proposed multiple times, but she always politely declined. Saying she was meant to be many things but a wife was not one of them.

The man with her is taller than her, but considering she is barely 5'5, that is no big feat. He has dark hair, and facial hair. He's dressed in dark trousers, black shoes with a matching belt, a button down shirt with a quarter zip pull-over on top, and a matching trench over-top. Basically, he looks like a model out of a j crew or banana republic catalog. He has a big watch on his wrist, which I assume she bought for him, as she always loved men's watches. They always reminded her of her grandfathers, and I had received three during our three years of marriage together. I still wear them today. He appeared a confident businessman, and I assumed he was successful, as she had become wildly successful. I knew she would be.

In our final face to face conversation I told her I admired her ambition stating "that's what I love about you, you go after what you want and never let anything stop you." And in fifteen years that hadn't changed. She was a top designer, still running her mothers firm as she had been for the past eighteen years. She was often quoted in the New York Times and Wall Street Journal regarding product launches and responses to vintage pieces. Feminists loved her, for she was the woman who defied all social norms. She established her career, wasn't married, and she chose not to have children.

There's another bet I would have placed everything on, and again would have lost. When we were together all she talked about was her desire to be a mother. She wanted two children, a boy and a girl, who she'd named after her father, and her stepfather. She talked about her dreams to take them to dance classes and lacrosse practice. Teach them how to read, paint, laugh, and love. She wanted to show them the world, and she wanted to be their world. She was the most maternal person I ever knew. Without a doubt she'd be an incredible mother. But she wasn't one.

There was still time. She was only 40. Women started families in their 40's all the time. But I knew her. If she wasn't a mother now, she wasn't ever going to be a mother. It was funny. When we were first together I had no desire to be a father. Which, she stated she didn't understand. I'd be a great father were her constant words to me. Overtime my feelings had changed. But I had only wanted her to be the mother of my children. And for a time that dream was to be a reality, until she collapsed in her office of exhaustion and miscarried. She barely survived the loss of her second child, but our marriage was not so lucky.

But I did become a father. I have a daughter, she's eight. And she in many respects is the true love of my life. My ex-wife and I share custody. Which, is how I ended up here. In the corner grocery store at nine o'clock on a Friday night, buying ice cream sundae supplies with my little girl, and running into the one who got away.

They were standing in the wine aisle. She's mentioning on how Serena won't like that vineyard, she's entirely too picky. His response is that she's too generous, wine is wine. She offers another label instead, same price. He says fine. He then states he's getting a bottle of scotch, is there something she'd like. She replies no, she'll have a drink at the bar later.

From the few context clues I assume they're about to go meet up with Serena and her husband. They're obviously visiting for the weekend, as she still resides in Paris. It's rumored she doesn't visit often but can't stand to sell her childhood home, as its one of the final things she has of her mother.

Before he walks away he kisses the side of her head and murmurs something to her. Probably an "I'll be right back", or a simple "I love you". A brief smile crosses her lips. In that moment I can tell she's happy. That the jcrew model makes her happy. That without the children she once spoke of, or the presence of her mother she still survived. That she doesn't have any regrets. That it's time for me to move on… to another aisle. And in that moment my vivacious daughter blows my cover "Daddy, I can't find the sprinkles!" Then she makes a glance in our direction. A glance that lands on me. She then becomes startled. And in an instant she recognizes me. And the memories begin to flood.

Our first time

Our rips to Paris

Our fights

Our reconciliation's

Our many breakups

Our Wedding

Our Numerous Schemes

Our Honeymoon

Our Valentines Day's

Our Divorce

About a year after our divorce I went to see her in Paris. I wanted to tell her how sorry I was that our marriage had ended. She asked me why we could never get it right. I told her it was nothing to do with her, I just didn't know how to be a husband. How to take away her pain. How to be the support system she deserved. That I knew there was a better man out there for her. And I thought it was the truth. Maybe it was at the time. But in reality it was a mistake. A mistake I still live to regret. For she was and still is my unattainable dream. And for a period of time I had the unattainable dream. But I was a young idiot, and I thought there was better out there for her than me. Before the conversation ended, she told me she understood, and that she hoped someday we would smile at each other and remember the life we shared together and in that moment we would congratulate each other on our new lives, on our dreams coming true.

It would have been easy to walk up to her after all these years and confess that I had made many mistakes, all beginning with her. Tell her we could have a fresh start. She could be a mother and I could get my valentine back. But I could tell through the brief interaction that she was happy, that she was accepting of her life, that she was in love. So instead I smiled at her. And in that smile I remembered a life shared when we were young, and sent her congratulations on her life, on her dreams that came true. She smiled back and mouthed "She's beautiful".

I place my hand on my daughters shoulder's and turned her around to leave the isle "Come on sweetheart, we'll go find the sprinkles." Glancing back one last time. Her husband has returned, and moved an arm around her waist, asking if she's okay. She says she's fine.

"Daddy"

"Yes?"

"Who was that lady?"

"Oh, just someone I knew another lifetime ago, that's all."

The End.


	2. Chapter 2

Once I got home I couldn't help but keep repeating the scene in my head over and over again. She was in town. She had been right in front of me. She was close enough to touch and yet still slipped through my fingers. She had moved on. The smart thing would be to accept that it had happened, and try to move on myself after all these years. But I couldn't. For fifteen years I had missed her. I had replayed moment after moment of our marriage in my head. The good memories are what got me through the lonely days.

At the start our marriage was pure bliss. Even with the loss of my father and the pain that it caused it was easy to survive because she was there, holding my hand through the service. Speaking on my behalf to lawyers and reporters. And when the gossip died down, our life began. It was the best time of my life.

We both worked long hours. We were committed to our work. We were young CEOs, we had to be. But we woke up in each other's arms, and fell asleep in them. When I had a business trip she designed in the hotel, and when she had fashion weeks in Milan, Paris, Rome then I'd acquired a new property in that area. We stole breaks during the day. A lunch here, a coffee break there, a private meeting booked on our calendars when the occasion permitted. Our evenings were spent at business dinners and charity events with her hand in mine under the table and my arm around her waist at the bar. The weekends were spent together. We'd walk Monkey in central park, watch old movies in bed, and have dinners in private corner booths. And I thought it would last forever, and it could have if I hadn't run away at the first sign of trouble.

A year and a half after we exchanged vows Blair found out she was pregnant. I was so excited. I couldn't wait to be father. I was scared; terrified actually. But with Blair as my child's mother, I knew all would be right. But Blair was in the middle of developing a fall line for New York Fashion Week. Her mother had officially retired and it was her first show as a lead designer and CEO of the business. She wanted to make her proud, and I couldn't deny her that satisfaction. I had spent my whole life wanting my father's approval, even from the grave. But she was overworked. She wasn't sleeping and could barely keep food down. I tried to get her to relax, help with the workload, but it wasn't enough. When she lost our child my world stopped and her world crashed. She had never looked more defeated and heartbroken. And I never felt more like a failure.

For the first few days after she was released from the hospital she locked herself in the Atelier. What she did I have no idea but her fashion show went off without a hitch that Saturday. It set a precedent that columnists still reference in fashion week reviews today. But she didn't walk the final runway, and she didn't do after show press interviews. Once the show was over she spent the next week in our townhouse locked in the bedroom crying. And I knew the only one who could put back the pieces was me. But I didn't know how. When she lost her first baby with Louis all I thought about was how I could protect her from the pain. That I could be the one that saved her. But when it happened the second time I was at a complete loss. My only job was to protect my family, and I couldn't do it. So instead of trying to care for my wife, I ran away. And this time I didn't leave a note.

I spent a month in China working till my fingers bled. And when I finally came home there were divorce papers on my desk in the study. Blair's belongings were gone and she moved back to her Mother's penthouse.

Had I been at my best I could have stopped it. Sent flowers, sent gifts. Sat out front her penthouse door till she talked to me. Stalked the lobby of the atelier and blocked her office door. Any disturbance to get her to talk to me. But I was mourning my child too. And selfish as I was, I felt like I needed time to wallow too. So instead I refused to sign the divorce papers for over a year. They were messengered to me at least ten times. But I always took them and sent them to the shredder. It wasn't till a note on her personal stationary arrived with the papers stating "I'm not mad at you and I don't hate you, I love you and I just need us to heal" that I finally signed the papers. A copy of them with the note is still kept in my personal safe, along with her engagement ring and wedding bands that she sent to be after the final time I saw her in Pairs. Our wedding anniversary is still the code to the safe.

And that is what caused the end to my second marriage. Caroline Alpine, an Acquisitions Lawyer who I met during a Merger with a small hotel chain based in Dubai. Caroline was a grateful distraction after I saw Blair for the last time in Paris. She was a true friend. She never pushed me to talk about the loss, never asked much of me to be quite honest. She knew about Blair and the divorce. It was all the tabloids talked about for a year. But that didn't matter to her. We never had the connection Blair and I had, but we had something, companionship is probably the best way to describe it. And for years we really were just friends. She dated, and I slept around. It wasn't until I read that Eleanor had died that everything changed.

She found me at my penthouse that night completely obliterated. But I wouldn't tell her why. Instead I slept with her. And then somehow that translated into a relationship. I should have told her the truth. That Eleanor was a friend of mine who still kept in touch. That she had been a wonderful mother in law. That knowing she was gone meant more pain for Blair, and Blair's pain was my pain. But Caroline looked so happy, and I just didn't want to disappoint another person. So for roughly a year we were together. I never planned on marrying her; I figured she'd get bored of me or frustrated with the lack of formal commitment and dump me. But then she got pregnant with Natasha, our daughter, and it was time to be a man. I married her on the beach in the Hamptons weeks later.

Being married again was nothing like how it was with Blair. It wasn't bad, but it was very different. The passion to be together all the time wasn't there. And Caroline wasn't the business woman Blair had been. She was committed but she didn't own her business trade, so the passion for it to succeed wasn't the same. Therefore, she didn't understand my need to be at the office all the time. We spent time together of course, but we didn't make time for one another like I had with Blair. And Caroline never appeared to mind. But as her due date approached she said things had to change when the baby came.

I thought it would be hard to add being a father to my priority list. But it was the easiest thing I had ever done. When Natasha was born, my life felt as complete as it could. Caroline and I were devoted parents. We stayed up with her, fed her, watched her crawl and take her first steps. As she got older we went to the park and spent evenings with her instead of society events. It was a nice life, and I was happy for the first time in years, but every once in a while I couldn't help but wonder what this life would have been like with Blair by my side instead of Caroline.

It wasn't until Caroline wanted to surprise me with the latest photo of Natasha in my wallet that everything crashed. She found a picture of Blair from our wedding day that I never removed. And she snapped. I guess she googled our wedding date because hours later I found her in my office with my safe open. The divorce papers, Blair's rings, numerous pictures, article clippings and Blair's note were skewed all over my desk. The thing was Caroline didn't look angry. She didn't yell. She didn't throw things. She just stood there defeated. And simply stated she wanted a divorce. This time I signed the papers the first time they arrived.

From then on I remained committed to my daughter. I spent every other weekend with her doing many of the same things I use to do with Blair. Walks in the park, movies, dinner were all done together. Yes the walks in the park were to the playground, the movies we watched were animated, and dinner together was normally at Serendipity, but it was still similar. And we are the best of friends. Natasha looks at me like I'm her hero. She calls for me when she's scared, she asks me to fix her toys, she says thank you in awe when I buy her new dresses. She tells me every last detail of every play date and her time at school. She loves me unconditionally. I do everything in my power not to disappoint her. I don't think I'd survive if she left me too.

"Daddy." Said a squeaky voice from the corner of the room dressed in a pink princess nightgown carrying a doll in her right and a blanket in her left.

"Yes, sweetheart?" I shifted in my office chair so she could come over and sit on my lap.

"Are you alright, you look sad." She said as she snuggled into me.

"I'm never sad when you're here. I'm just thinking." As I leaned my head into her dark brown hair and caught a whiff of her baby shampoo.

"About the lady in the store." I sat back and looked at her surprised by her perceptiveness.

"Yes. How did you get so smart?"

"From school." She said as she shrugged her shoulders nonchalantly, almost a "duh" response.

"Of course." I said in a half laugh.

"Why don't you invite her over to come play if you're thinking about her?" If only it was that simple. As a child if you miss someone you just invite them over to play. It's a simple question that takes no effort to ask. If only she knew how much guts it took to ask the older you got.

"Well, it's been a long time since she came over to play. I don't know if she'd want too." And it's the truth. She looked happy with her j-crew model.

"Just ask nicely. That's what I do when I want you or mommy to play with me, and it almost always works."

And just like that is eight year old daughter sparked an idea.

"That's good advice. I think I'll take you up on it. Tell me, how would you like to go to the park tomorrow; we'll have breakfast on our bench. Spend the day on the swings."

"That sounds great. Will your friend be there?" She liked Blair already. That was a good sign.

"I'll ask nicely."

"Okay. I can't wait."

"Well first you need sleep. Go on to bed, I'll be there in a minute to tuck you in."

"Okay Daddy." And then Natasha slid off my lap and out of my study, blanket and doll in hand.

I then reached for my phone and dial a number for my florist. Once upon a time I was a regular.

"Hi, this is Chuck Bass. Can I make an order to be delivered within the hour? I'll pay to have it rushed….. Yes….. A dozen pink peonies….. To the Waldorf penthouse. The address should still be on file …..Correct, a Ms. Blair Waldorf. … And the card should say "If I ask nicely will you meet me in the park. Once upon a time you said I do. I'll be there at nine, but won't leave till you arrive, so take your time." ….. Can you read it back to me?...Yes. Perfect. And can you call me back when Ms. Waldorf signs. I don't care what time….. Great. Thank You. "

And that's how you ask an adult to come over and play.

The End.


End file.
